Patent GB-960084-A (GB)
Title: Haloaralkyl biguanides
IPC: C11D1/00
Filed: 1962-01-11
Abstract: The invention comprises biguanides of the formula <FORM:0960084/C1/1> and their salts, wherein at least one of R1, R2, R3 and R4 is an "Arylkylene" group of 7-18 carbon atoms, in which the "Aryl" residue is a mono or poly carbocyclic or heterocyclic aryl nucleus (including mixed poly nuclei such as indene, and nuclei in which R1 and R2 or R3 and R4 are taken together as the alkylene group to form a heterocyclic ring such as tetrahydroisoquinolino or isoindolino) optionally bearing from 1 to 3 halogen, alkyl, alkoxy, aryl, aralkyl or alkaryl substituents and "alkylene" represents a straight or branched chain hydrocarbon group which may be substituted by alkyl, aryl or cyclo-alkyl groups, and any remaining symbols R1, R2, R3 or R4 represent hydrogen or an organic radical of 1-5 carbon atoms.  The biguanides are prepared by reacting the appropriate dicyandiamide R3 R4 N.C(:NH).NH.CN (obtained by known methods) with the salt of an amine R1R2NH.  The products are suitably converted into salts with hydrohalic, sulphuric, phosphoric, boric, phosphorous, sulphurous, sulphonic, nitric, nitrous or organic carboxylic acids or acidic compounds such as theophyllines and other purines, saccharine, phthalimide, benzoxazine-2,4-diones, N-p-methyl-benzenesulphonyl-N1-n-butyl urea, barbituric acids, mercaptobenzthiazole, 8-chlorotheophylline and succinimide. Suitably the "Arylalkylene" group may be a benzyl, phenylethyl, phenylpropyl, phenylbutyl, benzhydryl or 1-indanyl radical optionally bearing halogen, alkyl, alkoxy, aryl or aralkyl subtituents.  Triazines.-The products may be converted into dihydrotriazines, e.g. 1-p-chlorobenzyl-2-methyl-2-phenyl-1,2-dihydrotriazine, or into triazines, by reaction with organic acid esters or chlorides.ALSO:Germicidal and deodorant preparations comprising cosmetics, hair preparations, depilatories, detergents, antiperspirant compositions, dentifrices, lotions and pharmaceutical compositions contain as the germicidal constituent a biguanide of the formula <FORM:0960084/A5-A6/1> or a salt thereof, wherein at least one of R1, R2, R3 and R4 is an "arylalkylene" group of 7-18 carbon atoms in which the "aryl" portion is a mono or polycarbocyclic or heterocyclic aryl nucleus (including mixed poly nuclei such as indano and nuclei in which R1 and R2 or R3 and R4 are taken together as the alkylene group to form a heterocyclic ring such as tetrahydroisoquinolino or isoindolino) optionally bearing from one to three halogen, alkyl, alkoxy, aryl, aralkyl or alkaryl substituents, and "alkylene" represents a straight or branched chain hydrocarbon group which may be substituted by alkyl, aryl or cycloalkyl radicals, and any remaining symbols R1, R2, R3 and R4 represent hydrogen or an organic radical of 1-5 carbon atoms. The germicide is suitably employed in the form of its salts with organic or inorganic acids or acidic compounds such as theophyllines and other purines, saccharine, phthalimide, benzoxazine - 2,4 - diones, N , p - methylbenzenesulphonyl-N1-butyl urea, barbituric acids, mercaptobenzthiazole, 8 - chlorotheophylline and succinimide. The pharmaceutical preparations suitably take the form of tablets, solutions and elixirs and may contain other therapeutic compounds such as antihistamines, sulphonamides, lipotropic agents such as methionine, choline, isositol and beta-sitosterol, stimultants such as caffeine and amphetamines, analgesics such as codeine, aspirin and related compounds and phenacetin, laxatives, barbiturates, penicillin derivatives and other antibiotics, vitamins, hormones and antifungal agents.